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$49+ Cheap flights from Midway (MDW) to Oklahoma

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — OKC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Midway to Oklahoma

Cheapest flights from Midway to Oklahoma
Explore the most affordable flight options available from Midway to Oklahoma. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Frontier deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
-
DFW
1 stop8h 58m
Frontier
Sat 3/76:05 pm
DFW
-
MDW
Nonstop2h 16m
Frontier
Deal found 1/29$87
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:45 am
MDW
-
DFW
Nonstop2h 52m
Frontier
Thu 2/266:56 pm
DFW
-
MDW
Nonstop2h 16m
Frontier
Deal found 1/27$88
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:00 pm
MDW
-
DFW
Nonstop2h 46m
Frontier
Sun 3/810:30 pm
DFW
-
MDW
Nonstop2h 19m
Frontier
Deal found 1/27$89
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:45 am
MDW
-
DFW
Nonstop2h 52m
Frontier
Sat 2/211:00 pm
DFW
-
MDW
Nonstop2h 19m
Frontier
Deal found 1/27$90
This Trip.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
MDW
-
DFW
1 stop9h 13m
Frontier
Sat 2/281:00 pm
DFW
-
MDW
Nonstop2h 19m
Frontier
Deal found 1/28$96
This Expedia deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/199:05 am
MDW
-
DFW
1 stop7h 39m
Frontier
Sat 2/281:00 pm
DFW
-
MDW
Nonstop2h 19m
Frontier
Deal found 1/27$97
This Frontier deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:09 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Sun 5/108:03 pm
DFW
-
MDW
Nonstop2h 18m
Frontier
Deal found 1/26$98
This Frontier deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:09 pm
MDW
-
DFW
Nonstop2h 54m
Frontier
Sun 4/198:03 pm
DFW
-
MDW
Nonstop2h 18m
Frontier
Deal found 1/28$100
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 am
MDW
-
DFW
Nonstop2h 45m
Frontier
Sat 2/281:00 pm
DFW
-
MDW
Nonstop2h 19m
Frontier
Deal found 1/27$101
This Trip.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
-
DFW
1 stop9h 33m
Frontier
Sat 2/281:00 pm
DFW
-
MDW
Nonstop2h 19m
Frontier
Deal found 1/27$103
This Expedia deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/187:00 am
MDW
-
DFW
1 stop9h 13m
Frontier
Fri 2/2011:37 am
DFW
-
MDW
Nonstop2h 16m
Frontier
Deal found 1/28$104
This Expedia deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:15 am
MDW
-
DFW
1 stop8h 58m
Frontier
Mon 3/99:00 pm
DFW
-
MDW
Nonstop2h 20m
Frontier
Deal found 1/28$105

Find flight deals from Midway to Oklahoma

Keep the following information in mind while searching for Midway to Oklahoma flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$87
(Frontier)

One-way from

$49
(Trip.com)

Popular in

January

Cheapest in

October

Average price

$457

Good round-trip deal

$291 or less
Provider with most accurate pricing for Chicago (CHI)-Oklahoma City Will Rogers World flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Oklahoma City Will Rogers World flights.
Search Deals
From Chicago Midway to Oklahoma
Search Deals
One-way flight from Chicago Midway to Oklahoma
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Oklahoma.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Oklahoma that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Oklahoma that are best for you.

Fly from

Midway

Fly to

Oklahoma

Route

Depart

Return

Price

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Wed 3/11

11:25 am-2:08 pm

Nonstop2h 43m

Dallas/Fort Worth

Wed 3/18

8:00 am-10:25 am

Nonstop2h 25m

$97

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 2/26

3:00 pm-5:46 pm

Nonstop2h 46m

Dallas/Fort Worth

Thu 3/5

6:56 pm-9:12 pm

Nonstop2h 16m

$116

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Tue 3/3

7:30 am-4:15 pm

1 stop8h 45m

Dallas/Fort Worth

Wed 3/11

8:00 am-10:25 am

Nonstop2h 25m

$128

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Wed 2/18

7:00 am-4:13 pm

1 stop9h 13m

Dallas/Fort Worth

Thu 2/26

6:56 pm-9:12 pm

Nonstop2h 16m

$130

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 3/12

4:55 pm-7:38 pm

Nonstop2h 43m

Dallas/Fort Worth

Sun 3/15

6:00 am-10:19 pm

1 stop16h 19m

$160

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Mon 2/16

8:15 am-11:05 am

Nonstop2h 50m

Dallas/Fort Worth

Thu 2/19

6:56 pm-9:12 pm

Nonstop2h 16m

$160

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 2/12

3:00 pm-5:46 pm

Nonstop2h 46m

Dallas/Fort Worth

Fri 2/13

11:37 am-1:53 pm

Nonstop2h 16m

$170

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Tue 3/31

12:47 pm-8:59 pm

1 stop8h 12m

Dallas/Fort Worth

Tue 4/7

1:00 pm-5:54 pm

1 stop4h 54m

$177

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sat 2/28

6:00 am-12:36 pm

1 stop6h 36m

Dallas/Fort Worth

Sat 3/7

5:30 am-12:46 pm

1 stop7h 16m

$177

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Tue 3/10

10:45 am-5:37 pm

1 stop6h 52m

Dallas/Fort Worth

Tue 3/17

1:00 pm-5:54 pm

1 stop4h 54m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 60 results
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Best time to book a flight from Midway to Oklahoma

Have a flexible travel schedule? Discover the best time to fly to Oklahoma from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Oklahoma

What is the cheapest time of day to fly from MDW to OK?

Find hourly flight availability from Midway to Oklahoma. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

It’s optimal to fly from Chicago Midway Airport to Oklahoma in the afternoon. By choosing this option you can save up to 32% on the cost of your flight, compared to a flight in the evening.

What is the cheapest day to fly from Chicago Midway Airport to Oklahoma?

Use this chart to determine the cheapest time to fly round-trip from Midway to Oklahoma. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Oklahoma flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Oklahoma

Get insights into the airlines that provide service to Oklahoma. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Oklahoma. Reviews last updated January 29, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Oklahoma to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Midway to Oklahoma. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Oklahoma?

    Departing from Chicago Midway Airport to Oklahoma will take you 1h 55m. The distance between Chicago Midway Airport and Oklahoma is about 582 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chicago Midway Airport to Oklahoma?

    While some choose either Chicago Midway - Oklahoma City Will Rogers World or Chicago Midway - Fayetteville Northwest Arkansas, Chicago Midway - Dallas/Fort Worth is the most popular route from Chicago Midway Airport to Oklahoma.

  • What are the cheapest flights from Chicago Midway Airport to Oklahoma?

    The cheapest flight price from Chicago Midway Airport to Oklahoma is $213. On average you can expect to pay $395. The most popular route, (Chicago Midway - Dallas/Fort Worth), can usually be booked for $82.

  • Can I find deals for flights from Midway to Oklahoma that include hotel bookings?

    Yes. In addition to deals on Midway to Oklahoma flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Oklahoma?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Oklahoma.

  • Can I find deals for business class flights from Midway to Oklahoma?

    Yes. Cheapflights offers flight deals from Midway to Oklahoma by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Midway to Oklahoma

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Oklahoma

Discover the top airline that operate flights from Midway to Oklahoma. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$131Average$347FlexibilityNo cancel feeOn-time63%

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